A. Field of the Invention
This invention relates to 3-chloro-2-oxazolidinones useful in the art of chemistry and having antibacterial activity.
B. Description of the Prior Art
Walles U.S. Pat. No. 3,591,601 (patented July 6, 1971) discloses certain 3-halo-2-oxazolidinones having the formula: ##SPC1##
Where X is broadly defined as bromine or chlorine, and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are broadly defined, inter alia, as hydrogen or lower-alkyl containing from one to four carbon atoms. The compounds are said to be useful "in germicidal, bleaching, and chemical reaction applications."
While the above definitions are broadly embracive of compounds having a quaternary carbon at the 4- and/or 5-positions of the oxazolidinone ring, i.e., compounds where either each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is lower-alkyl or compounds where each of R.sub.1 and R.sub.2 or each of R.sub.3 and R.sub.4 is lower-alkyl (the other pair being hydrogen), such compounds are not specifically taught by Walles, who discloses only compounds where the 4- and 5-carbon atoms are either unsubstituted or where either one or both of the 4- and 5-carbon atoms bear a single lower-alkyl group. Thus, of the 2-oxazolidinones having the above general structure where each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are either hydrogen or lower-alkyl, Walles discloses only the following species. (The "Walles Cpd. Nos." are adopted here for reference purposes hereinafter.)
______________________________________ Walles Cpd. No. R.sub.1 R.sub.2 R.sub.3 R.sub.4 X ______________________________________ 1 CH.sub.3 H H H Cl 2 C.sub.2 H.sub.5 H H H Cl 3 H H H H Cl 4 CH.sub.3 H H H Br 5 CH.sub.3 H CH.sub.3 H Cl 6 C.sub.4 H.sub.9 H H H Br ______________________________________
Certain of the above-listed Walles compounds have been prepared and it has been found that they are somewhat unstable and consequently have limited usefulness as germicidal agents. On the other hand, it has been surprisingly found that certain compounds within the ambit of the very broad disclosure of the patentee, but not specifically contemplated thereby, are surprisingly stable, in contrast with the compounds actually prepared by Walles, and possess unexpected advantageous properties as germicides.